Dr. William Myers
Professor of Chemistry
Profile
Work in Professor Myers' laboratory is directed towards the synthesis of interesting and novel organic compounds using metal-mediated processes. In one major effort, involving a long-standing collaboration between the Myers lab and the lab of Prof. Dean Harman of the University of Virginia, Myers and his students work with electron-rich metal systems capable of binding to a carbon-carbon double bond in aromatic rings (benzene and benzene-related species, pyrroles, pyridines, furans, etc), disrupting the aromatic stabilization of the ring and making the ring susceptible to attack by reagents that normally would not react with such rings. In addition, the metal system blocks one face of the ring, so that such reactions yield stereospecific derivatives. Removal of these elaborated molecules from the metal gives products with potential utility as therapeutic medicines. In a second effort, Myers and his students collaborate with the lab of Prof. Gupton here at UR, in work that uses metal-based "cross-coupling" chemistry to convert carbon-halogen bonds (C-Cl or C-Br) to new carbon-carbon bonds, thus linking two separate molecular fragments into one new compound. Again, the products of these reactions have potential as medicinal drugs. As a synthetic group, much of our work involves conducting chemical reactions, isolating and purifying products, and acquiring characterization data to determine or confirm the structure and stereochemistry of these products. Nuclear Magnetic Resonance (NMR) spectroscopy gives us information about hydrogen, carbon, and phosphorus atoms in the chemicals with which we work as well as insights into their connectivity and spatial relationships, and Mass Spectrometry (MS) tells us about molecular composition. We use chromatographic techniques for separation and identification of products, in the form of GC-MS (gas chromatography-mass spec) and HPLC (high pressure liquid chromatography) instruments.
Publications
Articles
J.A. Pienkos, V.E. Zottig, D.A. Iovan*, M. Li*, D.P. Harrison, M. Sabat, L.J. Strausberg, V.A. Teran, W.H. Myers, and W.D. Harman  "Friedel–Crafts Ring-Coupling Reactions Promoted by Tungsten Dearomatization AgentOrganometallics, 2013, 32, 691-703.
L.J. Strausberg, M. Li, D.P. Harrison, W.H. Myers,  M. Sabat, and W.D. Harman  "Exploiting the o-Quinodimethane Nature of Naphthalene: Cycloaddition Reactions with Dihapto-coordinated Tungsten Naphthalene Complexes" Organometallics, 2013, 32, 915–925.
B. Quillian, E.E. Joslin, T.B. Gunnoe, M. Sabat, W.H. Myers   "2,2,2-Tris(pyrazolyl)ethoxide (EpOX) Ruthenium (II) Complexes, (EpOX)RuCl(L)(L′): Synthesis, Structure and Reactivity"  Inorganic Chemistry., 2013, 52, 1113–1121.
M.J. Pouy, S.A. Delp, J. Uddin, V.M. Ramdeen, N.A. Cochrane, G.C. Fortman, T.B. Gunnoe, T.R. Cundari, M. Sabat, and W.H. Myers   "Intramolecular Hydroalkoxylation and Hydroamination of Alkynes Catalyzed by Cu(I) Complexes Supported by N-Heterocyclic Carbene Ligands" ACS Catalysis, 2012, 2, 2182–2193.
E.E. Joslin, C.L. McMullen, T.B. Gunnoe, T.R. Cundari, M. Sabat, W.H. Myers    "Coordination Chemistry of 4-methyl-2,6,7-trioxa-1-phosphabicyclo[2,2,1]heptane: Preparation and Characterization of Ru(II) Complexes" Inorganic Chemistry, 2012, 51, 4791–4801.

D.P. Harrison, D.A. Iovan*, W.H. Myers, M. Sabat, S. Wang, V.E. Zottig, W.D. Harman   “[4+2] Cyclocondensation Reactions with Tungsten Dihydropyridine Complexes and the Generation of Tri- and Tetrasubstituted Piperidines”   Journal of the American Chemical Society, 2011, 133, 18378–18387.

D.P. Harrison, A.C. Nichols-Nielander*, V.E. Zottig, L.J. Strausberg, R.J. Salomon, C.O. Trindle, M. Sabat, T.B. Gunnoe, D.A. Iovan*, W.H. Myers, and W.D. Harman  "Hyper-Distorted Tungsten Allyl Complexes and their Stereoselective Deprotonation to Form Dihapto-Coordinated Dienes" Organometallics, 2011, 30, 2587–2597.
J.P. Burke, M. Sabat, W.H. Myers, J.J. Chruma,  "Unexpected exo selectivity for an intramolecular Diels-Alder reaction involving a doubly-activated δ-pentenolide dienophileTetrahedron:Asymmetry, 2011, 22, 31-35.
D.P. Harrison, M. Sabat, W.H. Myers, W.D. Harman, "Polarization of the Pyridine Ring: Highly Functionalized Piperidines from Tungsten-Pyridine ComplexJournal of the American Chemical Society, 2010, 132, 17282–17295.
J.A. Marshall, C.A. Griot, H.R. Chobanian, W.H. Myers, "Synthesis of a Lactone Diastereomeric of the Cembranolide Uprolide DOrganic Letters, 2010, 12, 4328-4331.
V.E. Zottig, M.A. Todd, A.C. Nichols-Neilander*, D.P. Harrison, M. Sabat, W.H. Myers, W.D. Harman, "Epoxidation, Cyclopropanation, and Electrophilic Addition Reactions at the meta-position of Phenol and meta-CresolOrganometallics, 2010, 29, 4793–4803.
J.P. Burke, M. Sabat, D.A. Iovan*, W.H. Myers and J.J. Chruma   "Exploring the Original Proposed Biosynthesis of (+)-Symbioimine: Remote Exocyclic Stereocontrol in a Type I IMDA ReactionOrganic Letters, 2010, 12, 3192–3195.
D.P. Harrison, G.W. Kosturko, V.M. Ramdeen, A.C. Nichols-Nielander*, M. Sabat, W.H. Myers, W.D. Harman  "Tungsten-Promoted Pyridine Ring Scission:  The Selective Formation of η2-Cyanine and η2-Merocyanine Complexes and their derivatives" Organometallics, 2010, 29, 1909-1915
R.J. Salomon, M.A. Todd, M. Sabat, W.H. Myers, W.D. Harman,  "Single and Double Electrophilic Addition Reactions to the Aniline Ring Promoted by a Tungsten π-Base", Organometallics, 2010, 29, 707-709.
K.D. Welch, D.P. Harrison, M. Sabat, E.Z. Hejazi*, B.T. Parr*, M.G. Fanelli*, N.A. Gianfrancesco*, D.S. Nagra*, W.H. Myers, W.D. Harman,  "Michael-Aldol Ring Closures with Dihapto-Coordinated Pyrrole Complexes and the Synthesis of Tetrahydroindole Cores" Organometallics, 2009, 28, 5960-5967.
D.P. Harrison, V.E. Zottig, G.W. Kosturko, K.D. Welch, W.H. Myers, W.D. Harman  "Stereo- and Regioselective Nucleophilic Addition to Dihapto-Coordinated Pyridine Complexes" Organometallics, 2009, 28, 5682-5690.
R. J. Salomon, E.C. Lis, M.U. Kasbekar*, K.C. Bassett, W.H. Myers, C.O. Trindle, M. Sabat, W.D. Harman  "Stereoelectronic Effects in Dihapto-coordinated Complexes of TpW(NO)(PMe3) and their Manifestation in Diels-Alder Cycloaddition of Arenes" Organometallics, 2009, 28, 4724-4734.
G.W. Kosturko, D.P. Harrison, M. Sabat, W.H. Myers, W.D. Harman  "SelectfluorTM Mediated Dialkoxylation of Tungsten η2-pyridinium Complexes"   Organometallics, 2009, 28, 387-389.
D.P. Harrison, K.D. Welch, M. Sabat, W.H. Myers, W.D. Harman,  "An Efficient Synthesis of an η2-Pyridine Complex and a Preliminary Investigation of the Bound Heterocycle's Reactivity"    Journal of the American Chemical Society, 2008, 130, 16844-16845.
E. Lis, R. Salomon, M. Sabat, W.H. Myers, W.D. Harman,  "Synthesis of 1-Oxadecalins from Anisole Promoted by Tungsten"   Journal of the American Chemical Society, 2008, 130, 12472-12476.
G.W. Kosturko, P.M. Graham, W.H. Myers, T.M. Smith, M. Sabat, and W.D. Harman  "Tungsten-Promoted Diels-Alder Cycloaddition of Pyridines: Dearomatization of 2,6-Dimethoxypyridine Generates a Potent 2-Azadiene Synthon"   Organometallics, 2008, 27, 4513-4522.
M.A. Todd, M. Sabat, W.H. Myers, T.M. Smith, W.D. Harman, "Stereoselective Umpolung Tandem Addition of Heteroatoms to Phenol"   Journal of the American Chemical Society, 2008, 130, 6906-6907.

M.A. Todd, W.H. Myers, M. Sabat, W.D. Harman, "[2+2] Cycloaddition Reactions with a Tungsten-Stabilized 2H-PhenolJournal of the American Chemical Society, 2007, 129, 11010-11011.

K.D. Welch, E.C. Lis, Jr., W. Liu, D.P. Harrison, R.J. Salomon, W.H. Myers,  and W.D. Harman   "Large-Scale Syntheses of Several Synthons to the Dearomatization Agent {TpW(NO)(PMe3)} and Convenient Spectroscopic Tools for Product Analysis"   Organometallics, 2007, 26, 2791-2794.
W. Liu, K. Welch, C.O. Trindle, M. Sabat, W.H. Myers, and W.D. Harman  "Facile Intermolecular Aryl-F Bond Cleavage in the Presence of Aryl C-H bonds: Is the 2-Arene Intermediate Bypassed?"   Organometallics, 2007, 26, 2589-2597.
D.A. Delafuente, G.W. Kosturko, P.M. Graham, W.H. Harman*, W.H. Myers, Y. Surendranath*, R.C. Klet*, C.O. Trindle, M. Sabat, and W.D. Harman   "Isomerization Dynamics and Control of the η2/N Equilibrium for Pyridine ComplexesJournal of the American Chemical Society, 2007, 129, 406-416.
Y. Surendranath*, W.H. Myers,  and W.D. Harman  "Tungsten Promoted Dearomatization of Heterocycles: Uncovering the Latent 2-Azadiene Character of Pyrimidines"    Organometallics, 2006, 25, 5852-5853.
K.D. Welch, P.L. Smith, A.P. Keller*, W.H. Myers, M. Sabat. W.D. Harman."Osmium(II)-, Rhenium(I)-, and Tungsten(0)-Promoted Dipolar Cycloaddition Reactions with Pyrroles: Exploiting the Azomethine Ylide Character of this HeterocycleOrganometallics, 2006, 25, 5067-5075.
E. Lis, W. Liu, M.A. Todd, W.H. Myers, D.A. Delafuente, Y. Lin, M. Sabat, C. Mocella, W.D. Harman  "The Uncommon Reactivity of Dihapto-Coordinated Nitrile, Ketone, and Alkene Ligands when Bound to a Powerful p-BaseOrganometallics, 2006, 25, 5051-5058.
M.A. Todd, M. Grachen*, W.H. Myers, W.D. Harman  "Common Electrophilic Addition Reactions at the Phenol Ring:  the Chemistry of TpW(NO)(PMe3)(η2-phenol)Organometallics, 2006, 25, 3948-3954.
K.C. Bassett, F. You, P.M. Graham, W.H. Myers, M. Sabat, W.D. Harman  "Furan [3+2] Dipolar Cycloadditions Promoted by a p-Basic Tungsten Metal Fragment"    Organometallics, 2006, 25, 435-439.
W.H. Myers, K.D. Welch, P.M. Graham, A.P. Keller*, M. Sabat, W.D. Harman   "Tungsten(0) and Rhenium(I) η2-Pyrrole Complexes:  Dearomatization of Pyrroles and their Facile Isomerizations, Protonations, and Reductions"  .Organometallics, 2005, 24, 5267-5279.
P.M. Graham, D.A. Delafuente, W.  Liu, W.H. Myers, M. Sabat, W.D. Harman   "Facile Diels Alder Reactions with Pyridines Promoted by Tungsten"   Journal of the American Chemical Society, 2005, 127, 10568-10572.
D.A. Delafuente, W.H. Myers, M. Sabat, W.D. Harman  "Tungsten(0) η2-Thiophene Complexes: Dearomatization of Thiophene and Its Facile Oxidation, Protonation, and HydrogenationOrganometallics200524, 1876-1885.

Education
Ph.D., University of Florida
B.A., Houston Baptist University
Contact Information
(804) 289-8249
(804) 287-1897 (Fax)
Areas of Expertise
Inorganic/Organometallic Chemistry